Jeff Holst and Jillian Sidoti, together or separately, on the stories that built Last Life Ever and the systems behind them. Conferences, podcasts, masterminds, mid-stage fireside chats, anywhere a room of curious people is gathered.
Jeff was diagnosed with leukemia at twenty seven, hiked Machu Picchu at thirty, and has not stopped since. He owns three hundred and fifty apartment units, ran a hundred-mile ultra last year, and is writing a book about it. He is the reason no one in his orbit gets to have a bad day.
Jillian spent twenty years as a securities attorney helping entrepreneurs raise more than four billion dollars. She sold her law firm in 2024 and moved her family to Rincón, Puerto Rico, because the math finally worked. She now runs the system that lets people fund a travel-first life without quitting their job or pretending they have it figured out.
We have spoken to rooms of real estate investors, securities attorneys, podcast audiences, and entrepreneurs who already know they want more and are looking for a hand on the shoulder pointing somewhere specific. The point of the talk is never the talk. The point is the conversation it kicks off, and the trip the audience books with themselves a week later.
Pick the topic that fits the room. Or tell us what your audience is wrestling with and we will shape the talk around it.
The promise behind Last Life Ever. How to stop saving travel for the calendar's edges and put it at the center of the system instead. Best for entrepreneurial and lifestyle audiences who already feel the pull and want a framework.
How to build the operating system that pays for the trips, the books, the moves, and the years off. We walk through real numbers from real companies and show the audience what is actually possible inside a normal workweek.
Jeff's keynote. Leukemia at twenty seven, Machu Picchu at thirty, and what happens when you build a philosophy that has no room for a bad day. The talk audiences come up to him after, with tears and stories of their own.
How Jeff went from bankruptcy at thirty seven to three hundred and fifty units by fifty, in a market most people gave up on. Practical, specific, and pointed at audiences ready to do the work without buying another guru course.
Twenty years of helping entrepreneurs raise four billion dollars, distilled into the rules that actually matter. Best for real estate operators, fund managers, and founders who want to raise without making the mistakes that cost everyone else their reputation.
The math, the conversations, and the year-long sequence behind selling a twenty-year law practice, moving the family to Puerto Rico, and rebuilding the work on the other side. Best for audiences thinking about their own exit and trying to figure out what comes after.
We have done all of these. Pick what works for your event.
Real estate associations, securities and investment conferences, podcasts, masterminds, and entrepreneurial conferences across the U.S.
Full list available on request.
The more I learn about Jeff's life and his infectious positive mindset the more convinced I am that he needs to share his story with the world.
Vinney Chopra · Author & multifamily investorJillian is just amazing. I went in, unscrewed the top of my head and she just poured knowledge into it until it was overflowing. Incredible amount of in-depth information presented by a real expert.
Dan M. · Capital-raising workshop attendeeI stand by every word. Your book will change every life who reads it. All my love to you Jeff.
Dr. Jaml Saycon · Author endorsementA short form. We respond within two business days with availability, fee range, and the next step.